Water → HCID 11632832, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-Chloro-2-(2-chloro-pyridin-4-yl)-3-[1-(4-methoxy-3-trifluoromethyl-phenyl)-2,5-dimethyl-1H-imidazol-4-yl]-propenal (0.9 g, 1.9 mmol) in 8 mL THF was dropped to a cold (0° C.) suspension of potassium tert-butoxide (0.47 g, 4.2 mmol) in 4 mL THF and water (0.04 mL, 2.1 mmol). The light brown reaction mixture was stirred at 0° C. for 1 hr. The reaction was extracted two times with ethyl acetate, saturated NaHCO3− solution, water and brine. The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product was purified by chromatography on silica gel (n-heptane/ethyl acetate 90:10→0:100) to obtain the desired product as a white solid (0.15 g, 19%), MS: m/e=406.2 (M+H+).

Provenance & Evidence